CN1044473C - 用作抗菌的环庚三烯酮取代的苯基唑烷酮 - Google Patents
用作抗菌的环庚三烯酮取代的苯基唑烷酮 Download PDFInfo
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- CN1044473C CN1044473C CN93120887A CN93120887A CN1044473C CN 1044473 C CN1044473 C CN 1044473C CN 93120887 A CN93120887 A CN 93120887A CN 93120887 A CN93120887 A CN 93120887A CN 1044473 C CN1044473 C CN 1044473C
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- China
- Prior art keywords
- oxo
- methyl
- phenyl
- oxazolidinyl
- ethanamide
- Prior art date
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- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 title abstract description 10
- 239000003242 anti bacterial agent Substances 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 119
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 107
- -1 phenyl-2-oxo-5-oxazolidinyl Chemical group 0.000 claims description 56
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 40
- 125000003368 amide group Chemical group 0.000 claims description 34
- 125000003282 alkyl amino group Chemical group 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- CQIICFKQUKFATJ-UHFFFAOYSA-N n-[[2-oxo-3-[4-(5-oxo-4-pyrrolidin-1-ylcyclohepta-1,3,6-trien-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(N3CCCC3)=CC=2)C=C1 CQIICFKQUKFATJ-UHFFFAOYSA-N 0.000 claims description 2
- PJHKRWSGGZHJAJ-UHFFFAOYSA-N n-[[2-oxo-3-[4-[5-oxo-4-(prop-2-enylamino)cyclohepta-1,3,6-trien-1-yl]phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(NCC=C)=CC=2)C=C1 PJHKRWSGGZHJAJ-UHFFFAOYSA-N 0.000 claims description 2
- JYZHRFBLIUHHCY-UHFFFAOYSA-N n-[[3-[4-(4-morpholin-4-yl-3-oxocyclohepta-1,4,6-trien-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C2=CC(=O)C(N3CCOCC3)=CC=C2)C=C1 JYZHRFBLIUHHCY-UHFFFAOYSA-N 0.000 claims description 2
- IVFIPQUFGHWPOM-UHFFFAOYSA-N n-[[3-[4-[4-(cyclopropylamino)-5-oxocyclohepta-1,3,6-trien-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(NC3CC3)=CC=2)C=C1 IVFIPQUFGHWPOM-UHFFFAOYSA-N 0.000 claims description 2
- XYDKNGGJJIDBCL-UHFFFAOYSA-N n-[[3-[4-[4-(diethylamino)-5-oxocyclohepta-1,3,6-trien-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=CC(=O)C(N(CC)CC)=CC=C1C1=CC=C(N2C(OC(CNC(C)=O)C2)=O)C=C1 XYDKNGGJJIDBCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- MBOLZYXPULTDAO-SFHVURJKSA-N n-[[(5s)-3-[3-fluoro-4-(4-morpholin-4-yl-5-oxocyclohepta-1,3,6-trien-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(N3CCOCC3)=CC=2)C(F)=C1 MBOLZYXPULTDAO-SFHVURJKSA-N 0.000 claims 2
- ADXUEFFNOMMQQT-UHFFFAOYSA-N methyl 2-[[2-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-5-oxocyclohepta-1,3,6-trien-1-yl]amino]acetate Chemical compound C1=CC(=O)C=CC(C=2C=CC(=CC=2)N2C(OC(CNC(C)=O)C2)=O)=C1NCC(=O)OC ADXUEFFNOMMQQT-UHFFFAOYSA-N 0.000 claims 1
- MDMFDQRZUQFKBM-UHFFFAOYSA-N n-[[2-oxo-3-[4-(5-oxo-4-piperazin-1-ylcyclohepta-1,3,6-trien-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(N3CCNCC3)=CC=2)C=C1 MDMFDQRZUQFKBM-UHFFFAOYSA-N 0.000 claims 1
- CQXCEEABNMRESO-UHFFFAOYSA-N n-[[2-oxo-3-[4-[3-oxo-4-(prop-2-ynylamino)cyclohepta-1,4,6-trien-1-yl]phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C2=CC(=O)C(NCC#C)=CC=C2)C=C1 CQXCEEABNMRESO-UHFFFAOYSA-N 0.000 claims 1
- SZZBGOCIGMSCAJ-UHFFFAOYSA-N n-[[3-[4-[4-(2-hydroxyethylamino)-5-oxocyclohepta-1,3,6-trien-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(NCCO)=CC=2)C=C1 SZZBGOCIGMSCAJ-UHFFFAOYSA-N 0.000 claims 1
- OFNDZJKNRQBNCS-UHFFFAOYSA-N n-[[3-[4-[4-(2-methoxyethoxy)-5-oxocyclohepta-1,3,6-trien-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=CC(=O)C(OCCOC)=CC=C1C1=CC=C(N2C(OC(CNC(C)=O)C2)=O)C=C1 OFNDZJKNRQBNCS-UHFFFAOYSA-N 0.000 claims 1
- KDWVYBGMRDQXFC-UHFFFAOYSA-N n-[[3-[4-[4-(cyclopentylamino)-5-oxocyclohepta-1,3,6-trien-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C1=CC=C(C=2C=CC(=O)C(NC3CCCC3)=CC=2)C=C1 KDWVYBGMRDQXFC-UHFFFAOYSA-N 0.000 claims 1
- KAKXRVVBBNLNRY-UHFFFAOYSA-N n-[[3-[4-[4-(methylamino)-5-oxocyclohepta-1,3,6-trien-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=C(O)C(=N/C)/C=CC(C=2C=CC(=CC=2)N2C(OC(CNC(C)=O)C2)=O)=C1 KAKXRVVBBNLNRY-UHFFFAOYSA-N 0.000 claims 1
- QVWDCTQRORVHHT-UHFFFAOYSA-N tropone Chemical group O=C1C=CC=CC=C1 QVWDCTQRORVHHT-UHFFFAOYSA-N 0.000 abstract description 26
- 239000000543 intermediate Substances 0.000 abstract description 25
- 238000000034 method Methods 0.000 abstract description 24
- 239000004599 antimicrobial Substances 0.000 abstract description 3
- 230000008029 eradication Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 174
- 238000006243 chemical reaction Methods 0.000 description 88
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
- 239000000243 solution Substances 0.000 description 80
- 239000007787 solid Substances 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- 239000011734 sodium Substances 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- 238000005406 washing Methods 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 16
- 239000012266 salt solution Substances 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 238000005660 chlorination reaction Methods 0.000 description 14
- 238000001035 drying Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000007872 degassing Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 10
- 235000010446 mineral oil Nutrition 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 6
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- WHUOJOBYLUYPHQ-UHFFFAOYSA-N 5-phenyl-2h-1,3-oxazol-2-id-4-one Chemical compound O=C1N=[C-]OC1C1=CC=CC=C1 WHUOJOBYLUYPHQ-UHFFFAOYSA-N 0.000 description 5
- YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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|---|---|---|---|
| US98858992A | 1992-12-08 | 1992-12-08 | |
| US988,589 | 1992-12-08 | ||
| US6635693A | 1993-05-21 | 1993-05-21 | |
| US066,356 | 1993-05-21 |
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| Publication Number | Publication Date |
|---|---|
| CN1092413A CN1092413A (zh) | 1994-09-21 |
| CN1044473C true CN1044473C (zh) | 1999-08-04 |
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|---|---|---|---|
| CN93120887A Expired - Fee Related CN1044473C (zh) | 1992-12-08 | 1993-12-08 | 用作抗菌的环庚三烯酮取代的苯基唑烷酮 |
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|---|---|
| CN (1) | CN1044473C (enrdf_load_stackoverflow) |
| IL (1) | IL107663A (enrdf_load_stackoverflow) |
| MX (1) | MX9307705A (enrdf_load_stackoverflow) |
| MY (1) | MY117563A (enrdf_load_stackoverflow) |
| PH (1) | PH31085A (enrdf_load_stackoverflow) |
| TW (1) | TW299332B (enrdf_load_stackoverflow) |
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|---|---|---|---|---|
| CN104327007B (zh) * | 2014-10-20 | 2016-07-27 | 安徽师范大学 | 3,4,5-三取代噁唑烷酮类化合物及其制备方法 |
| CN107118173B (zh) * | 2017-07-12 | 2019-10-29 | 阿里生物新材料（常州）有限公司 | 一种环庚三烯并噁嗪类化合物及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3149608A1 (de) * | 1981-12-15 | 1983-08-04 | Dr. Madaus & Co, 5000 Köln | Substituierte tropolone, verfahren zur herstellung derselben und diese enthaltende pharmazeutische zubereitungen |
| EP0127902A2 (en) * | 1983-06-07 | 1984-12-12 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| EP0316594A1 (en) * | 1987-10-21 | 1989-05-24 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
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1993
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- 1993-11-03 PH PH47191A patent/PH31085A/en unknown
- 1993-11-18 IL IL10766393A patent/IL107663A/en not_active IP Right Cessation
- 1993-11-29 MY MYPI9302517 patent/MY117563A/en unknown
- 1993-12-07 MX MX9307705A patent/MX9307705A/es not_active IP Right Cessation
- 1993-12-08 CN CN93120887A patent/CN1044473C/zh not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3149608A1 (de) * | 1981-12-15 | 1983-08-04 | Dr. Madaus & Co, 5000 Köln | Substituierte tropolone, verfahren zur herstellung derselben und diese enthaltende pharmazeutische zubereitungen |
| EP0127902A2 (en) * | 1983-06-07 | 1984-12-12 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| EP0316594A1 (en) * | 1987-10-21 | 1989-05-24 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
Also Published As
| Publication number | Publication date |
|---|---|
| PH31085A (en) | 1998-02-05 |
| MY117563A (en) | 2004-07-31 |
| IL107663A (en) | 1996-10-16 |
| CN1092413A (zh) | 1994-09-21 |
| MX9307705A (es) | 1994-06-30 |
| TW299332B (enrdf_load_stackoverflow) | 1997-03-01 |
| IL107663A0 (en) | 1994-02-27 |
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